#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/67/1556799.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1556799
loop_
_publ_author_name
'Aakeröy, Christer B'
'Spartz, Christine L.'
'Dembowski, Sean'
'Dwyre, Savannah'
'Desper, John'
_publ_section_title
;
 A systematic structural study of halogen bonding versus hydrogen bonding
 within competitive supramolecular systems.
;
_journal_issue                   'Pt 5'
_journal_name_full               IUCrJ
_journal_page_first              498
_journal_page_last               510
_journal_paper_doi               10.1107/S2052252515010854
_journal_volume                  2
_journal_year                    2015
_chemical_formula_moiety
;
(C6 H Br F4 O)2 (C12 H12 N2)
;
_chemical_formula_sum            'C24 H14 Br2 F8 N2 O2'
_chemical_formula_weight         674.19
_chemical_name_systematic
;
SD-1--20-12--5, 4-Br---F4-PhOH, 1,2-bis(4-pyridyl)ethane
;
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.464(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.9125(16)
_cell_length_b                   4.6925(3)
_cell_length_c                   20.0909(12)
_cell_measurement_reflns_used    4226
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.42
_cell_measurement_theta_min      2.32
_cell_volume                     2375.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11464
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         32.57
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    3.502
_exptl_absorpt_correction_T_max  0.5410
_exptl_absorpt_correction_T_min  0.4197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.885
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.946
_refine_diff_density_min         -0.966
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         4064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                3044
_reflns_number_total             4064
_reflns_threshold_expression     >2sigma(I)
_publcif_datablock.id            {4b955d6b-e817-46e8-8329-eb0fed9fa672}
_cod_data_source_file            lc5065.cif
_cod_data_source_block           BrF4OH11
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/IUCr/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1556799
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br -0.024830(8) 1.28914(6) 0.063810(12) 0.02760(9) Uani 1 1 d .
N11 N 0.16779(8) 0.2178(4) 0.30189(10) 0.0251(4) Uani 1 1 d .
C12 C 0.21757(8) 0.1194(6) 0.31417(12) 0.0261(5) Uani 1 1 d .
H12 H 0.2395 0.1757 0.2846 0.031 Uiso 1 1 calc R
C13 C 0.23829(9) -0.0591(6) 0.36761(12) 0.0270(5) Uani 1 1 d .
H13 H 0.2738 -0.1245 0.3744 0.032 Uiso 1 1 calc R
C14 C 0.20734(8) -0.1444(5) 0.41189(11) 0.0238(4) Uani 1 1 d .
C15 C 0.15549(9) -0.0415(6) 0.39870(13) 0.0309(5) Uani 1 1 d .
H15 H 0.1327 -0.0938 0.4274 0.037 Uiso 1 1 calc R
C16 C 0.13768(9) 0.1363(6) 0.34377(13) 0.0306(5) Uani 1 1 d .
H16 H 0.1022 0.2041 0.3353 0.037 Uiso 1 1 calc R
C17 C 0.22955(9) -0.3300(5) 0.47264(12) 0.0262(5) Uani 1 1 d .
H17A H 0.2465 -0.4994 0.4575 0.031 Uiso 1 1 calc R
H17B H 0.2003 -0.3968 0.4927 0.031 Uiso 1 1 calc R
C21 C 0.11859(8) 0.7168(5) 0.17233(11) 0.0217(4) Uani 1 1 d .
O21 O 0.15971(6) 0.5547(4) 0.20005(9) 0.0277(4) Uani 1 1 d .
H21 H 0.1541(11) 0.455(7) 0.2344(15) 0.033 Uiso 1 1 d .
C22 C 0.12267(8) 0.9117(5) 0.12212(12) 0.0241(4) Uani 1 1 d .
F22 F 0.16889(5) 0.9300(4) 0.10234(8) 0.0337(3) Uani 1 1 d .
C23 C 0.08128(8) 1.0840(5) 0.09105(11) 0.0232(4) Uani 1 1 d .
F23 F 0.08858(6) 1.2668(3) 0.04240(8) 0.0311(3) Uani 1 1 d .
C24 C 0.03295(8) 1.0692(5) 0.10859(11) 0.0226(4) Uani 1 1 d .
C25 C 0.02791(8) 0.8774(5) 0.15865(11) 0.0223(4) Uani 1 1 d .
F25 F -0.01835(5) 0.8531(4) 0.17655(7) 0.0302(3) Uani 1 1 d .
C26 C 0.06948(8) 0.7066(5) 0.18980(11) 0.0216(4) Uani 1 1 d .
F26 F 0.06272(5) 0.5159(3) 0.23689(7) 0.0291(3) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C16 N11 C12 117.8(2) . .
N11 C12 C13 122.8(2) . .
N11 C12 H12 118.6 . .
C13 C12 H12 118.6 . .
C12 C13 C14 120.0(2) . .
C12 C13 H13 120.0 . .
C14 C13 H13 120.0 . .
C13 C14 C15 117.0(2) . .
C13 C14 C17 121.3(2) . .
C15 C14 C17 121.7(2) . .
C16 C15 C14 119.4(2) . .
C16 C15 H15 120.3 . .
C14 C15 H15 120.3 . .
N11 C16 C15 123.1(2) . .
N11 C16 H16 118.5 . .
C15 C16 H16 118.5 . .
C14 C17 C17 111.7(3) . 7_546
C14 C17 H17A 109.3 . .
C17 C17 H17A 109.3 7_546 .
C14 C17 H17B 109.3 . .
C17 C17 H17B 109.3 7_546 .
H17A C17 H17B 107.9 . .
O21 C21 C22 119.8(2) . .
O21 C21 C26 124.5(2) . .
C22 C21 C26 115.8(2) . .
C21 O21 H21 112.0(19) . .
F22 C22 C23 118.8(2) . .
F22 C22 C21 118.7(2) . .
C23 C22 C21 122.5(2) . .
F23 C23 C22 118.61(19) . .
F23 C23 C24 120.5(2) . .
C22 C23 C24 120.9(2) . .
C25 C24 C23 117.7(2) . .
C25 C24 Br1 120.71(16) . .
C23 C24 Br1 121.50(17) . .
F25 C25 C26 119.1(2) . .
F25 C25 C24 119.7(2) . .
C26 C25 C24 121.12(19) . .
F26 C26 C25 119.56(19) . .
F26 C26 C21 118.4(2) . .
C25 C26 C21 122.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C24 1.868(2) .
N11 C16 1.330(3) .
N11 C12 1.338(3) .
C12 C13 1.369(3) .
C12 H12 0.9500 .
C13 C14 1.388(3) .
C13 H13 0.9500 .
C14 C15 1.394(3) .
C14 C17 1.501(3) .
C15 C16 1.375(3) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 C17 1.534(5) 7_546
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C21 O21 1.322(3) .
C21 C22 1.384(3) .
C21 C26 1.397(3) .
O21 H21 0.87(3) .
C22 F22 1.350(2) .
C22 C23 1.372(3) .
C23 F23 1.346(3) .
C23 C24 1.379(3) .
C24 C25 1.378(3) .
C25 F25 1.334(2) .
C25 C26 1.371(3) .
C26 F26 1.343(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O21 H21 N11 0.87(3) 1.73(3) 2.556(3) 158(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
C16 N11 C12 C13 -0.1(4) .
N11 C12 C13 C14 -0.2(4) .
C12 C13 C14 C15 0.3(4) .
C12 C13 C14 C17 -177.4(2) .
C13 C14 C15 C16 -0.1(4) .
C17 C14 C15 C16 177.6(3) .
C12 N11 C16 C15 0.4(4) .
C14 C15 C16 N11 -0.2(4) .
C13 C14 C17 C17 69.4(3) 7_546
C15 C14 C17 C17 -108.2(3) 7_546
O21 C21 C22 F22 0.4(3) .
C26 C21 C22 F22 -179.3(2) .
O21 C21 C22 C23 179.5(2) .
C26 C21 C22 C23 -0.2(4) .
F22 C22 C23 F23 -0.6(3) .
C21 C22 C23 F23 -179.7(2) .
F22 C22 C23 C24 178.7(2) .
C21 C22 C23 C24 -0.3(4) .
F23 C23 C24 C25 179.8(2) .
C22 C23 C24 C25 0.5(4) .
F23 C23 C24 Br1 2.4(3) .
C22 C23 C24 Br1 -176.91(18) .
C23 C24 C25 F25 -179.1(2) .
Br1 C24 C25 F25 -1.6(3) .
C23 C24 C25 C26 -0.2(4) .
Br1 C24 C25 C26 177.27(18) .
F25 C25 C26 F26 0.9(3) .
C24 C25 C26 F26 -178.0(2) .
F25 C25 C26 C21 178.5(2) .
C24 C25 C26 C21 -0.4(4) .
O21 C21 C26 F26 -1.5(4) .
C22 C21 C26 F26 178.2(2) .
O21 C21 C26 C25 -179.1(2) .
C22 C21 C26 C25 0.5(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168305958
